Vacationing down south or buying a place down south

Wife likes water so she would prefer florida. We visited her cousin a couple times in St. Petersburg, did some touring even made it to Key West. Could see ourselves getting something down there. Lots to do,golf,beaches,spring training baseball and even hockey games in Tampa.
We wanna tour Costa Rica and Panama soon.

My retirement place will be my ass plunked in my mobile cabin (if it’s even done by then! lol) overlooking my valley paradise. I have no desire to go somewhere hot and crowded, I can’t swim so water isn’t a drawing card. The thought of moving somewhere far away doesn’t excite me at all, being far away from family. I have been fortunate to have 95% of my family within an hour’s drive so don’t want to move away from them all, of course that could change as I get older and grumpier.

I am in full agreement with kevlar. I really hate leaving the yard in general let along going on this thing called a holiday(need to look that up lol). Now if I had the desire to go anywhere for winter it would be Costa Rica. A hay farmer I know rents on the northern tip somewhere and for 1500CAD/month you live like a king. I am not sure about the temp, but he is a big guy and in 20C weather he is dripping so it can't be too bad. The guy is on a plane Nov 1 and back April 30 like clockwork for the last 10 years.

If I was looking for beachfront retirement I would pick a Caribbean island. Nicest one I have been to was Martinique but since I don't speak fluent French I would have to say Barbados is a very close second. Cabo San Lucas is nice because it's always sunny and less expensive(or was 8 years ago when I was there). I don't think I would pick a US coastal area because they are just too crowded. 

But to me a secluded area with a mountain view would be perfect, something in Wyoming, Montana or maybe Idaho would be nice. Little warmer than here in the winter, but still get the seasons.

gleanerl that would probably be a lot more economical in Northern Saskatchewan.

You just have to get the rumour out there that it had been a toxic waste dump and would cost more money to clean up then the land is worth, they are trying to get the land sold before anyone finds out. ( just trying to help your retirement dream come true LOL )

Been to Costa Rica one year then Belize another. They are similar but I would likely choose Belize. I don't care for the ocean and beach for vacationing and neither does the wife. We prefer exploring, seeing different things, just generally being out and about in the land vs looking at or being in water. So in both those countries we liked being in the mountain areas more. There are some nice chunks of land available when doing an internet search. If I was to sell the farm this winter and then have nothing to do I would be buying a chunk of land down in Belize and building a house and other things. Don't see myself on an island sitting around. I would rather be on a mainland where I can get to a hardware store and keep building/developing things on the property. English is the official language in Belize and uses the $us for currency so easy for a vacationer to get around there.

Lots of countries to go see but I don't like leaving the farm much so on one hand the idea of renting a place works so a person is free to go elsewhere. But my tendency to stay on the farm also says owning my own property in another country and calling it home and parking my butt there is also a valid option.